Reaction of 1,4-bis(trimethylsilyl)-2-butene with aromatic aldehydes catalyzed by TiCl4: an approach to (1-vinylallyl)benzene type derivatives |
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Authors: | Qianqian Ding Maurice Santelli |
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Institution: | Université Paul Cézanne, Faculté des Sciences et Techniques de Saint-Jérôme, Laboratoire de Synthèse Organique, associé au CNRS UMR 6180, Avenue Normandie-Niemen, 13397 Marseille Cedex 20, France |
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Abstract: | 1,4-bis(Trimethylsilyl)-2-butene 1 can react with alkyl and aromatic aldehydes in the presence of titanium tetrachloride to give α-(trimethylsilyl)methyl homoallylic alcohols and (1-vinylallyl)benzene type compounds in poor to good yield according to the related position of each substituents present on the aromatic ring. In the last case, the reaction involves a type electrophilic substitution of 1,4-bis(trimethylsilyl)-2-butene by aromatic aldehydes activated by TiCl4, followed by a 1,2-migration of a vinyl group. |
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